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C0567

Sigma-Aldrich

(−)-Catechin

≥97% (HPLC), from green tea

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Synonym(s):
(−)-trans-3,3′,4′,5,7-Pentahydroxyflavane, (2S,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
Empirical Formula (Hill Notation):
C15H14O6
CAS Number:
18829-70-4
Molecular Weight:
290.27
EC Number:
242-611-7
MDL number:
MFCD00135997
UNSPSC Code:
12352200
PubChem Substance ID:
24892260
NACRES:
NA.77

biological source

green tea

Quality Level

200

Assay

≥97% (HPLC)

form

powder

storage temp.

2-8°C

SMILES string

O[C@@H]1Cc2c(O)cc(O)cc2O[C@H]1c3ccc(O)c(O)c3

InChI

1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m1/s1

InChI key

PFTAWBLQPZVEMU-HIFRSBDPSA-N

Gene Information

human ... BACE1(23621)

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General description

Catechins are major flavonoids present in green tea accounting to 90%. (−)-catechin is comparatively less bioavailable than the (+)-catechin for intestinal absorption.

Application

(-)-Catechin has been used:
  • to test its binding affinity towards estrogen receptor
  • as a reference standard in high-performance liquid chromatography for quantification of polyphenols from plant extracts (HPLC)
  • as a reference standard in kinetic studies to quantify antioxidants from Iranian green tea leaves

Biochem/physiol Actions

Catechins have wide biological functionality. They induce antiviral and anticancer activities. Catechins also play a key role in regulating carbohydrate and lipid metabolism. It prevents fat accumulation.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ji Hyung Jun et al.
Nature plants, 4(12), 1034-1043 (2018-11-28)
Proanthocyanidins (PAs) are primarily composed of the flavan-3-ol subunits (-)-epicatechin and/or (+)-catechin, but the basis for their different starter and extension unit compositions remains unclear. Genetic and biochemical analyses show that, in the model legume Medicago truncatula, two 2-oxoglutarate-dependent dioxygenases
(+)-Catechin is more bioavailable than (-)-catechin: relevance to the bioavailability of catechin from cocoa
Donovan JL, et al.
Free Radical Research, 40(10), 1029-1034 (2006)
Estrogen-like effects of wine extracts on nitric oxide synthesis in human endothelial cells
Simoncini T, et al.
Maturitas, 70(2), 169-175 (2011)
Green tea catechins: Their use in treating and preventing infectious diseases
Reygaert WC
BioMed Research International, 2018 (2018)
Rajapandiyan Krishnamoorthy et al.
Biomolecules, 9(12) (2019-12-11)
Human gut microbes are a profitable tool for the modification of food compounds into biologically active metabolites. The biological properties of catechins have been extensively investigated. However, the bioavailability of catechin in human blood plasma is very low. This study
View All Related Papers

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